Sodium Hydroxide → 1-Methyl-5-(3-benzoylpropyl)thio-1,2,3,4-tetrazole

HRID 1758313Notes

Reaction equation

HRID 1758313 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].NC(N)=[S:15].[CH3:17][N:18]1[C:22](Cl)=[N:21][N:20]=[N:19]1.[OH-].[Na+]>C(O)C>[CH3:17][N:18]1[C:22]([S:15][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:21][N:20]=[N:19]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 2535334-ChlorobutyrophenoneHCID 2723790ThioureaHCID 205098305-chloro-1-methyl-1H-1,2,3,4-tetrazole

Product 1

HCID 130916251-Methyl-5-(3-benzoylpropyl)thio-1,2,3,4-tetrazoleYield 11.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chlorobutyrophenone (1.8 g) and thiourea (0.8 g) is dissolved in ethanol (50 ml) and the solution is refluxed for 2 hours. To the mixture are added 1-methyl-5-chloro-1,2,3,4-tetrazole (1.2 g) and 10% aqueous sodium hydroxide (5 ml) and the mixture is further refluxed for 3 hours. Ethanol is distilled off and water is added to the residue. The mixture is extracted with chloroform. The chloroform solution is washed with water and saturated aqueous sodium chloride and dried over magnesium sulfate. Chloroform is distilled off. The residue is purified by column chromatography (Wakogel C-200, eluatn: chloroform) and the product is recrystallized from methanol-water to obtain 1-methyl-5-(3-benzoylpropyl)thio-1,2,3,4-tetrazole (0.3 g) as colorless needles, m.p. 57.5°-58° C.

Workup

  1. temperaturethe solution is refluxed for 2 hours
  2. temperaturethe mixture is further refluxed for 3 hours
  3. distillationEthanol is distilled off
  4. additionwater is added to the residue
  5. extractionThe mixture is extracted with chloroform
  6. washThe chloroform solution is washed with water and saturated aqueous sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. distillationChloroform is distilled off
  9. customThe residue is purified by column chromatography (Wakogel C-200, eluatn: chloroform)
  10. customthe product is recrystallized from methanol-water

Sources & evidence

ORD record
ord-97ad9bf006f345d38a9d1cca2d09653d
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

Loading…